Hydrochloric Acid → HCID 21849551, compound

HRID 862819Notes

Reaction equation

HRID 862819 reaction equation
C([NH:4][C:5]([CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1)([CH2:8][OH:9])[CH2:6][OH:7])(=O)C.[OH-].[Na+].Cl>CO>[NH2:4][C:5]([CH2:10][CH2:11][CH2:12][C:13]1[CH:14]=[CH:15][C:16]([N+:19]([O-:21])=[O:20])=[CH:17][CH:18]=1)([CH2:6][OH:7])[CH2:8][OH:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21849383HCID 21849383, compound

Product 1

HCID 21849551HCID 21849551, compoundYield 29.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Acetamido-2-[3-(4-nitrophenyl)propyl]-1,3-propanediol (400 mg) was dissolved in 50 ml of methanol and 6.7 ml of a 1N aqueous-sodium hydroxide solution was added thereto. The mixture was refluxed under heating for 3 hours and neutralized with dilute hydrochloric acid. The solvent was distilled away and chloroform was added to the residue for extraction. The chloroform layer was washed and dried, and the solvent was distilled away. The residue was purified by silica gel column chromatography (methanol:chloroform=1:4) to give 100 mg of 2-amino-2-[3-(4-nitrophenyl)propyl]-1,3-propanediol as a red, oily substance.

Workup

  1. temperatureThe mixture was refluxed
  2. temperatureunder heating for 3 hours
  3. distillationThe solvent was distilled away
  4. additionchloroform was added to the residue for extraction
  5. washThe chloroform layer was washed
  6. customdried
  7. distillationthe solvent was distilled away
  8. customThe residue was purified by silica gel column chromatography (methanol:chloroform=1:4)

Sources & evidence

ORD record
ord-ef00ea52fcdc47a3bed659ad20810eb1
Source dataset
uspto-grants-1998_02
Patent number
US05719176

Reaction notes

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